N,N{40 -bis(p-phenoxycarbophenyl)sulfondiamide

ABSTRACT

WHEREIN R1 represents a hydrogen atom, an alkyl group or an acetyl group, R3, R4, R5 and R6 are the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group or an alkoxy group having up to 12 carbon atoms or an aryl group, n being 1 or 2 and, when n 1,R2 a hydrogen atom, an alkyl group, an acyl group having up to 20 carbon atoms, a substituted or non-substituted aroyl group, a phenoxy carbonyl group or a substituted or non-substituted benzene sulfonyl group and, when n 2,R2 is a sulfonyl, carbonyl or dioxaloyl group or a group having the formula   where Z represents a phenylene group or an alkylidene group having up to 12 carbon atoms. Many of the compounds within this general formula are novel per se, and accordingly are claimed as such. Ultraviolet light stabilized polymers having incorporated therein a stabilizing amount of a compound having the general formula:

United States Patent [191 Havinga et al.

[ 1 N,N '-BIS( P-PHENOXYCARBOPHENYL)SUL- FONDIAMIDE [75] Inventors: Reginoldus Havinga, Schalkhaar;

Pieter Dirk Swaters, Lochem, both of Netherlands [73] Assignee: Koninklijke Industrieele Maatschappij Noury &Van der Lande N.V., Deventer, Netherlands I 22 Filed: July 6,1973

21 Appl. No.: 377,095

Related U.S. Application Data [62] Division of Ser. No. 67,588, Aug. 27, 1970, Pat. No.

[30] Foreign Application Priority Data OTHER PUBLICATIONS I-Ieacock et al., J. Chem. Soc. (1954), pp. 2481-2484. Wagner et al., Synthetic Organic Chemistry, Wiley & Sons, Inc., NY. (1965), PP. 822, 823.

Primary Examiner lohn F. Terapane Attorney, Agent, or Firm-Stevens, Davis, Miller &

Mosher 1451 Sept. 16, 1975 ABSTRACT Ultraviolet light stabilized polymers having incorporated therein a stabilizing amount of a compound having the general formula:

wherein R represents a hydrogen atom, an alkyl group or an acetyl group, R R R and R are the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group or an alkoxy group having up to 12 carbon atoms or an aryl group, n being 1 or 2 and, when n 1, R 21 hydrogen atom, an alkyl group, an acyl group having up to 20 carbon atoms, a substituted or nonsubstituted aroyl group, a phenoxy carbonyl group or a substituted or non-substituted benzene sulfonyl group and, when n 2, R is a sulfonyl, carbonyl or dioxaloyl group or a group having the formula where Z represents a phenylene group or an alkyli clene group having up to 12 carbon atoms. Many of the compounds within this general formula are novel per se, and accordingly are claimed as such.

1 Claim, No Drawings N,N -BIS( P-PHENOXYCARBOPHENYL )SULFON- DIAMIDE This is a division of application Ser. No. 67,588, filed Aug. 27, 1970, now US. Pat. No. 3,809,707.

The present invention relates to ultraviolet light stabilizers, that is to say, compounds which provide stabilization against the deteriorative effects of ultraviolet light, and provides a new class of such compounds and processes for their preparation. The present invention also relates to processes for preparing stabilized polymers by means of the novel compounds according to the invention and of related compounds. Moreover, the invention relates to novel stabilized compositions.

It is known that polymers, such as polyethylene, polypropylene, polyisobutylene, copolymers of ethylene with higher alkenes such as propylene and butylene or with vinyl acetate, polystyrene, polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with vinylidene chloride, polyvinyl acetate, polyester resins, polyurethanes, cellulose derivatives and other polymeric materials, may undergo degradation under the influence of ultraviolet light; this degradation takes the form of deterioration of the physical properties and/or of the color of the polymers.

It has now been found that this degradation may be reduced, or avoided, by incorporating in the polymers a stabilizing amount of one or more previously unknown compounds according to this invention, having the general formula:

wherein R represents a hydrogen atom, an alkyl group or an acetyl group, R and R are the same or different and each represents a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group having up to 12 carbon atoms or an aryl group, R and R are the same or different and each represents a hydrogen atom, a halogen atom, a hydroxy group, an alkyl or alkoxy group having up to 12 carbon atoms or an aryl group, n being I or 2 and, when n 1, R is an acyl group having up to carbon atoms, a substituted or non-substituted aroyl group, a phenoxy carbonyl group or a substituted or non-substituted benzene sulfonyl group and, when n 2, R is a sulfonyl, carbonyl or dioxaloyl group or a group having the general formula where Z is a phenylene group or an alkylidene group having up to 12 carbon atoms.

Examples of novel compounds acccording to the above formula are: 1. phenyl-N-acetyl-anthranilate 2. phenyl-p-N-acetyl aminobenzoate 3. phenyl-pN-acryloyl-aminobenzoate phenyl-N-tosyl-anthranilate phenyl pN-tosyl-aminobenzoate ptert.butylphenyl-N-acetyl-anthranilate p-nonylphenyl-N-acetyl-anthranilate p-chlorophenyl-N-acetyl-anthranilate p-phenylphenyl-N-acetyl-anthranilate m-hydroxyphenyl-N-acetyl-anthranilate phenyl-N-nonanoyl-anthranilate phenyl-p-N-nonanoyl-am nobenzoate phenyl-N-stearoyl-anthranilate m-hydroxyphenyl-N-nonanoyl-anthranilate phenyl-m-N-acetyl-aminobenzoate phenyl-N-benzoyl-anthranilate phenyl-m-N-tosyl-aminobenzoate m-octoxyphenyl-N-acetyl-anthranilate l9. phenyl-p-N-( 4-dodecylbenzene-sulfonyl- )aminobenzoate 20. phenyl-N-(4-chlorobenzoyl )anthranilate 2 l. phenyl-N-(4-cyanobenzoyl )anthranilate 22. phenyl-N-( 2-methoxybenzoyl )anthranilate 23. phenyl-N-(3-isopropylbenzoyl)anthranilate 24. phenyl-N-(4-tert.butylbenzoyl)anthranilate 25. phenyl-N-methyl-N-acetyl-anthranilate 26. 2-chloro-4-phenylphenyl-N-acetyl-anthranilate 27. 2,4,5-trichlorophenyl-N-acetyl-anthranilate 28. p-nonylphenyl-N-tosyl-anthranilate 29. N,N-bis(o-phenoxycarbophenyl)urea 30. N,N-bis(o-phenoxycarbophenyl)oxalyl-diamide 31. N,N'-bis(o-phenoxycarbophenyl )adipoyl-diamide 32. N,N-bis(p-phenoxycarbophenyl)sulfon-diamide 33. N,N-bis(m-phenoxycarbophenyl)adipoyl diamide 34. N,N '-bis( o-phenoxycarbophe nyl )te rephthaloyldiamide 35. N,N"bis(o-phenoxycarbophenyl)dodecanedioyldiamide 36. N,N-bis[2-(4-tert.butylphenoxycarbo)phenyl- ]adipoyl-diamide 37. N,N'-bis[2-(4-nonylphenoxycarbo)phenyl]adipoyl-diamide 38. N,N-dimethyl-N,N-bis(o-phenoxycarbophenyl- )adipoyl-diamide 39. phenyl-N,N-diacetyl-anthranilate 40. phenyl-N-phenoxycarbo-anthranilate 41 p-tert.octylphenyl-N-acetyl-anthranilate 42. p-dodecylphenyl-N-acetyl-anthranilate 43. N-(2-phenoxycarbo)phenyl-N'-phenyl-urea 44. phenyl-N-hexyl-N-acetyl-anthranilate These compounds and the compounds 45. phenyl-p.N,N-dimethyl-amino-benzoate 46. p-tert.butylphenyl-anthranilate 47. m-hydroxyphenyl-anthranilate 48. phenyl-N-methyl-anthranilate 49. phenyLp-amino benzoate are referred to below, for convenience, by the numbers given in the left column.

The novel compounds of the general formula I may be prepared, in accordance with another aspect of this invention, by reacting a compound having the general formula:

with a compound having the general formula:

III

where R R R R and R have the meanings previously defined and A is a halogen atom or a hydroxy group, II preferably being an aminobenzoyl chloride, in an aqueous medium or an organic solvent, isolating the resultant compound of the formula:

and converting it into an acid amide or a sulfonamide of formula I. l

The reaction is preferably carried out in the presence of analkaline compound at a temperature from 0C. to the boiling point of the solvent. Suitable solvents include benzene, dioxane, ethylene glycol dimethyl ether, chloroform, carbon tetrachloride, hexane and petroleum ether. If the aminobenzoyl chloride and the phenol, i.e., the compounds of formulae II and III, are reacted in an organic solvent, pyridine, triethylamine and sodium carbonate may be used as alkaline compounds. The acid chloride, II, may be added per se or dissolved, preferably in the same solvent. If this reaction takes place in water, sodium hydroxide, potassium hydroxide, ammonium hydroxide or a water-soluble amine may also be used. The acid chloride is then added to the phenolic solution per se or dissolved in an organic solvent such as ethylene glycol dimethyl ether, dioxane or other water-miscible organic solvent.

Compounds according to the present invention wherein the amino group is in the ortho position relative to the ester carbonyl group may be advantageously obtained by starting from compounds having the general formula:

wherein R represents hydrogen or alkyl. The reaction with a phenol may be carried out in a solvent, e.g., dioxane, acetone, dimethyl sulfoxide, or tetrahydrofurane, in the presence of an alkaline compound such as potassium hydroxide or sodium hydroxide. While the carbon dioxide is escaping, compounds are formed having the general formula:

The compounds of the formulae IV and VI may be isolated from the reaction mixture by removing the solvent used, e.g., by decantation, filtering or distillation.

After purification by appropriate methods, these compounds may be characterized by determining their physical constants such as melting point, refractive index and their characteristic infrared absorption bands.

Preferred reaction components which may be used include alkylated or non-alkylated isatoic anhydrides, alkylated or nonalkylated aminobenzoic acids and aminobenzoyl chlorides, phenol, p-tert.-butylphenol, p-nonylphenol, pchlorophenol, p-dodecylphenol, pphenylphenol, resorcinol and meta'octyloxyphenol.

The aminobenzoyl chlorides to be used may be obtained in known manner by reacting the corresponding acids with chlorinating agents, such as POCl PCI PCI or SOCl The conversion of the compounds of the formulae IV and VI to the corresponding acid amides or sulfonamides may be carried out in a dry solvent, such as benzene, carbon tetrachloride, chloroform, petroleum ether, hexane, diethyl ether, ethylene glycol dimethyl ether, dioxane, ethyl acetate or n-butyl acetate, preferably in the presence of an alkaline substance such as an amine, e.g. pyridine or triethylamine.

As acylating or sulfonating agents, there may be used acetyl chloride, acryloyl chloride, n-nonanoyl chloride, stearoyl chloride, benzoyl chloride, substituted benzoyl chloride, p-toluene sulfonyl chloride, terephthaloyl chloride, sulfuryl chloride, oxaloyl chloride, succinoyl chloride, dodecanoic dichloride; phosgene and phenylchloroformate. Ketene or acetic anhydride may also be used as acetylating agents. After purification by appropriate methods, the acylated or sulfonated compounds may be characterized by determining their physical constants such as melting point or refractive index or their characteristic infrared absorption bands.

In addition to the novel compounds according to the invention, phenyl p-aminobenzoate, as described in Farmaco Ed. Sci. 12 (1957); phenyl anthranilate, as described in US. Patent No. 3,123,631; phenyl N- methyl anthranilate, as described in J. Org. Chem. 24, 1214 I959); phenyl p-N,N-diethyl-aminobenzoate, as described in German Patent No. 1,1 15,252; p-alkyl phenylanthranilate, as described in US. Pat. No. 2,776,959; and p-alkyl phenyl-p-aminobenzoate, as described in French Pat. No. 1,253,378 may also be used in order to reduce or avoid the degradation of polymers by ultraviolet light. In this literature, it is not mentioned that these compounds may be used for avoiding degradation of polymers.

Consequently, the invention also relates to the stabilization of polymers with the aid of compounds having the general formula I, wherein R to R,; have the meanings given and wherein R and R can each additionally represent an alkoxy group having up to 12 carbon atoms and wherein, when n 1, R can additionally represent a hydrogen atom or an alkyl group.

For use as UV. absorbers, the compounds according to the present invention may be homogeneously incorporated in the polymers to be stabilized, if desired in the presence of other additives, e.g., plasticizers, pig- 5 3 3 ments, heat stabilizers and lubricants, by known techmques such as roller mixing. They are preferably mcor- Yield 995% porated 1n the polymer in amounts of 0.1 5% by M, 784906 i h (NH hand 3.(X)

l The following examples and tables illustrate the 1n- 10 charm IR abs (czo ester band 585 vention. Where in these examples and tables reference is made to characteristic infrared absorption bands, (C=O amide band these are expressed in microns.

Starting from phenyl anthramlate, m an analogous EXAMPLE] way, the following compounds were obtained having 84.9 g of isatoic anhydride (96%), 47.0 g of phenol, general formula: 1.63 g of KOH and 500 ml of acetone .were heated under reflux for 2.5 hours. After cooling, the reaction Q o vn c mixture was poured into water, the precipitate was 20 drawn off by suction and dried. 105.5 of phenyl anthranilate were obtained. MR2

TABLE 1 Yield Part I M. P. acylating agent or P (NH! hand 232/292 sulfonating agent solvent base duct Charact. lR abs. I

(C=O ester band 5.90 p-toluene sulfonyl chloride acetone pyridine 4) (tosyl chloride) n-nonanoyl chloride chloroform l l benzoyl chloride stearoyl chloride (l3) p-chlorohenzoyl chloride pyridine (20) 21.3 g of the phenyl anthramlate obtamed, 8.64 g of m isopmpylbcnzoyl chloride H n (23) acetyl chloride (95%) and 400 ml of n-hexane were o-methoxybenzoyl chloride (22) p-cyanobenzoyl chloride (2l heated under reflux for 3 hours. After cooling the mixpmmhmylbemofl chloride (24) ture, the precipitate was drawn off by suction. 25.4 g phenylchlowfvrmuw -z Q-r q- 0) t g of compound (1 were obtained, having the formula: phcnyhwgydmte bcnzme TABLE 2 Part 2 characteristic physical IR absorption Prod- R2 constants bands UCI ( 4) SO C H CH;,p M.P. NH 3.0];

226229C.() C O ester 5.89;

S O 7.4l/8.62/l0.85 l l) COC,,H, n liquid n,,*" NH 2:99;

l.5453 C O ester 5.89; C O amide 5.9l (l6) COC;;H;, M.P. NH 3.00;

l66-l68.5C. C 0 ester 5.92;

C O amide 5.99 13 COC, H,- n M.P. NH 2.99;

5 l53C. C O ester 5.90;

C O amide 5.90 (20) COC.;H Clp M.P. NH 3.03;

l30.5-l32.5C. C O ester 5.99;

C O amide 5.99 23) COCGH M.P. NH 2.99;

123l24.5C. C O ester 5.90;

C O amide 5.99 (22) COC,;H,,OCH;,0 M.P. NH 3.03;

9293.5C. C O ester 5.82;

C 0 amide 6.08 (21) COC,;H CNp M.P. NH 3.05;

l66-l68C. C O ester 5.96;

C= O amide 6.00; C N 4.50 24 COC.;H;C(CH ,);,-p M.P. NH 3.03;

l l4-l 17C C O ester 5.90;

C O amide 6.0]

TABLE 2 Continued Part 2 characteristic IR absorption bands physical Prodconstants M.P. 97.5+98C.

C=O ester 5.91;

C O amide 5.7I

43 CONHC,,H,, M.P. NH 3.04;

C O ester 5.86;

C O amide 6.01

EXAMPLE II 27.4 g of p-aminobenzoic acid were heated under reflux with 100 ml of thionyl chloride for 2 hours and then the excess thionyl chloride was distilled off under reduced pressure. The crude p-aminobenzoyl chloride was incorporated in 100 ml of dry benzene and added to a suspension of 23.2 g of sodium phenolate in 250 ml of dry benzene. The mixture was heated under reflux for 2 hours and, after cooling, treated with water and a saturated soda solution. After drying the benzene I Yield (NH band Charact. IR abs.

(C=O ester band 5.78

IC=O amide band 5.97

Starting from phenyl-m-aminobenzoate, in an analogous way, compound 15) was obtained, having the formula:

solution was saturated with hydrogen chloride gas. The TI precipitate .of. phenyl-p-aminobenzoate hydrochloride o obtained was centrifuged off. From the solid phase, 42.0 g of phenyl-p-aminobenzoate was obtained with I the aid of bicarbonate. HIT

" c=o Y CH3 Yield ,m Yield 95% M. P. l68-l7lC. MP. l34-l35C.

. (NH: hand ass 2.95 (NH band 2.94 Char-act. IR abs. Charact. IR abs.

(C=O ester band 5.88 (C=O ester hand 5.82 In an analogous way phcnyl-m-aminobcnzoatc was obtained. Yield I 85% lC==O amide band 5.90 M. P. 45.5-46.5C.

(N band 9 Starting from the mor p-ammobenzoate, in an anal- Chumul- IR g ogous way, the following compounds were obtained (C=O cstcr band 21.3 g of the phenyl-p-aminobenzoate so obtained were reacted with acetyl chloride in chloroform as solvent in the way described in Example I. 24.0 g of compound (2) were obtained. having the formula:

having the general formula:

VIII

Table 2 Part I acylating agent or sulfonating agent solvent base product acryloyl chloride chloroform 3) p-toluene sulfonyl chloridediethylcther pyridine 5) n-nonanoyl chloride chloroform (l2) p-dodccylbcnzene sulfonyl ethylene glycol pyridine l9) chloride dimethyl ether p-tolucnc sulfonyl chloride diethylcther pyridine l7) p-dodccyl- TABLE 2 Part 2 characteristic physical lR absorption Prod- R constants bands UCI ( 3) COCHzCH, M.P. NH 2.93;

l l5-l20C. C I O ester 5.79;

C umide 5.99; C 0 6. l0 SO C H CH M.P. NH 3.00;

226229C. C O ester 5.8 l;

S 0 7.45/8.60/l0.92 (l2) COC H,-,-n semi-solid NH 2.99;

product C I O ester 5.80;

C O amide 6.04 (l9) so c H.c,.,H M.P. NH 3.02;

l32l40C. C O ester 5.80;

s 0 7.5 l/8.65/l0.95 (l7) SO C H CH M.P. NH 3.07;

l39-l40C. C O ester 5.75;

S O 7.5 l/8.70/l0.98

EXAMPLE "I TABLE 3 8.1 g of isatoic anhydride, 11.0 g of p-nonylphenol and 1.1 g of NaOl-l were heated under reflux in 50 m1 Pan 2 of dioxane for 6 hours. After cooling, the reaction mixris i ture was oured into water. 16.3 of -non l hen l Physical 1R absotpfimq p g p y p y R, constants bands anthranllate were obtained, having the formula:

pC(CH M.P. l38-l40C. NH 2.85 293;

. C O estcr 5.88 'mOH M.P. l7l-l74C.- NH 28512.95:

I 4 C O ester 5.98; OH 2.95

o c 5 p-Cl M.P. 79-s0.5c. NH 290 100; C O' ester 5.88 p--C.;H;-, M.P. 142-145C. NH 2.85 295;

C O ester 5.94 2-c1 4- c..H M.P. 1u7 109c. NH ass/2.9x;

C=Ocstcr 5.96 2,4 5.Cl M.P. l29-l3lC. NH. 2.83/193; C=Oestcr 5.85

I 20 Yield mOC H -n Ii uid n NH. lets/2.95; Ch t [R b 185/294 8 195370 c ='o 0M9! 5.90

a .C M. l22-l24C. 2.88 2.97;

(c=o ester band 5.89 p C(Gm- HQCHH" P g 5.90

40 C H. waxy product NH: 185/194; Starting from other substituted phenols, in an analo- C o gous way, the following compounds were obtained, having the general formula: I

EXAMPLE IV 14.5 g of p-nonyl phenylanthranilate and 4.7 g of acetyl chloride were heated under reflux in 100 ml of chloroform for 3 hours. After cooling and washing with 3 water, the solvent was distilled off. 13.4 g of compound 5 Ix (7) were obtained, having the formula:

' -c-0- -C,,H,,,

TABLE 3 HN HH Part I substituted phenol solvent anthranilate 354 .1

(NH band 3.02 ptertbutyldioxane p-terLbutylphenyl- I C 1R resorcinol dioxane m-hydroxyphenyl- (C=0e 1r b d 590 i p-chlorodioxane p-chlorophenylv PP y dioxane P-P y p y (c=o amide hand 5.96 lchloro-4-phenyldioxane (2 chl0ro-4-phenyl)phenyl- 1 2 4 5-trichlorodioxane 2,4.5-trichlorophenylm-(n-mctoxydioxane m-(n-)octoxyphenyl- Starting from the substituted phenyl anthramlates. F ptmmlylphenyl described in Example III, the following compounds dioxane p-dodecylphenylwere obtained having the general formula:

R Yield 91% MP. 6667C. o (NH band 2.90

Charact. lR uhs.

x c R (C=O ester band 5.9]

5 o I I a a Starting from N-hexyl tsatoic anhydrlde, m an analo- 2 3 4 gous way, phenyl-N-hexyl anthranilate, having the formula Xl (R C H was obtained. TABLE 4 Part 1 Liquid product n 1.5660 acylating agent or (NH band 2 5 sulfonating agent solvent base product Chumc! IR (C=O ester band 5.94 acetyl chloride chloroform 6) (l0) l5 1: :1 g g; a nmonanoyl chloride pyridine (l 4) 2.27 g of the phenyl N-methyl-anthrantlate obtained, acetyl chloride (26) 0.86 g of acetyl chlor1de, 0.83 g of pyridine and 35 ml kcwnc benzene 'f' of dry chloroform were heated under reflux for 3 hours. p-tolucnesulfonyl chloride dicthyl ether pyridine (28) After the solvent had been evaporated, washed and f6- cctyl fihlonde ff P f crystallized from hexane, 2.47 g of compound (25) having the formula below (R, CH were obtained:

TABLE 4 l I Part 2 1 R2 R5, physical characteristics IR product constants absorption bands 6) cocH pC(CH M.P. NH 3.03;

l63l65C. C O ester 5.90;

C O amide 5.98 (10) COCH m-OH M.P. NH 3.05;

l74l 77C. C 0 ester 5.90;

C 0 amide 6.00; OH 3.05 8) COCH p-Cl M.P. NH 3.00

l071llC. C 0 ester 5.89; C 0 amide 5.92 9 COCH pC H,, M.P. NH 3.02;

l73.5-l75.5C. C 0 ester 5.90;

C 0 amide 5.99 (l4) COC,.H;,-n m-OH liquid NH 3.00;

. e C 0 ester 5.88;

C O amide 5.90; OH 3.00 (26) COCH 2 C|-4 C.,H M.P.. NH 2.99;

|42-l44.5C. C 0 ester 5.85;

C 0 amide 5.92 27 COCH 2,4,5 Cl M.P. NH 2.99;

I t l40l43.5C. C 0 ester 5.88; t C=O amide 5.91 (l8) COCH 'm-0C,.H,,-n M.P. NH 3.00;

s 424-46C. C 0 ester 5.89;

C 0 amide 5.95 (28) s0 C..H.,CH; p-C H- M.P. NH 3.09;

V l()7-l 10C. C 0 ester 5.93;

v r s 0 7.50/8.60 /l0.85 41 COCH -C CH CH C CH., M.P. NH 3.03;

l68l7()C. C 0 ester 5.90;

C O amide 5.98 42 COCH -C.. H M.P. NH 3.00;

65-67C. C O ester 5.86; I C =0 amide 5.93

EXAMPLE V l 23.0 g of N-methyl isatolc anhydnde. 12.2 g of phe- -C -0- no] and 1.1 g of powdered NaOH were heated in 45 ml of dioxane for 4 hours at 45C. After cooling, the reaction mixture was poured into water. The precipitate RI'N CCHH was drawn off by suction, washed and recrystallized from an ethanol-water mixture in a ratio of 4:1. 26.8 g of phenyl-N-methyl anthranilate, having the formula Yield 92% w CH, w r M.P. 176-178C. belo (R e e obtained (C=O ester band 578 O Charact. lR abs.

H 5 (C=O amide band 6.05 CO: XI

analogous y. mpound (44) of formula x11 (R, C H was obtained.

Starting from phenyl-N-hexyl anthranilate, in an TABLE Liquid product n 1.5372

(C=O ester band 5.78 Fun I Churact. IR abs.

(C20 amde band 6 acylating agent or 5 sulfonating agent solvent base product phosgene diethyl ether pyridine (29) EXAMPLE VI oxalyl chloride chloroform (30) adipoyl chloride (31 Ketene was passed into a solution of 21.3 g of phenyl dwecmo'c d'chkmde (35 anthranilate, prepared in the way described in Example l, and 100 mg of p-toluene sulphonic acid in boiling toluene for 45 minutes. After the solvent had been evapo- TABLE 5 rated and recrystallized from a mixture of acetone and hexane in a ratio of 1:1, 13.3 g of compound (39) of 5 Part2 formula XII (R CH CO) were obtained.

physical characteristic IR product R2 constants absorption bands 29 Co M.P. NH 3.00; Yield 5% 173-177C. C 0 ester 5.90; M P, 8587C. C O amide 5.90

iC=O cster band 5.83 I Churuct. IR abs. (30) CO.C'O M.P. NH 3.05;

lC=o amide band 5.91 281-283.5C. C o ester 5.84;

(decomp.) C O amide 5.90

31 CO(C 2). C0 M.P. NH 3.00; l26-l30C I C O ester 5.88; EXAMPLE V11 I C o amide 5.92 8.5 g of phenyl anthranilate, prepared in the way de- (35) CO(CH- .)...CO M.P. NH 3.00;

0 scribed in Example I, 4.1 g of terephthaloyl chloride, 56 5 8; and 4.8 ml of pyridine were heated under reflux in chloroform for 4 hours. After cooling, the precipitate 30 was drawn off by suction, washed with hydrochloric acid and water and recrystallizedl figom Ci'llOl'OfOl'lTl. EXAMPLE vm 10.1 of com ound (34) avin t e ormu a:

g p g 6.81 g of phenyl-N-methyl anthtanilate, prepared in 35 the way described in Example V, 2.75 g of adipoyl H 9 (3 H A chloride and 5 ml of pyridine were heated under reflux N C c N in 50 ml of chloroform for 4 hours. After cooling. the. solution was washed with hydrochloric acid and then c=o '0 with water to neutrality. After the solvent had been I y I 40 evaporated, petroleum ether was added and then the o 0 precipitate formed was drawn off by suction and dried.

5.50 g of compound (38) having the formula:

were obtained.

I I O O l were obtained:

Yield M. P. l4()l45(..

(C=O ester hand 5.8l Charuct. lR abs.

(C=O amide band 6.08

EXAMPLE IX 5.0 g of phenyl-m-aminobenzoate, obtained in the way described in Example II, 2.15 g of adipoyl chloride and 5 ml of pyridine were heated under reflux in,50 ml of chloroform for 4.5 hours. After cooling, the solution was washed with dilute hydrochloric acid and subsequently with water and a sodium bicarbonate solution to neutrality. After the solvent had been dried and dis tilled off, the residue was incorporated in benzene, decolorized with carbon and again precipitated with petroleum ether. After filtration, 4.25 g of compound (33) having the general formula below were'obtained:

Starting from phenyl-p-aminobenzoate and sulfonyl chloride, in an analogous way, compound 32) having the formula:

were obtained.

M. P. 22 l-224C.

(NH band 2.90 Char-act. IR abs. I

i IC=O ester band EXAMPLE X H (i H ("=0 XIV l l v Yield 72% M.P. i l35l38C.

(NH hand 2.99 Charuct. IR abs.

(C=O ester band 5.85 (CO amide band 5.97

Starting from p-tert.butyl-phenyl-anthranilate, in an analogous way, compound (36) of formula XIV (R (CH C) was obtained.

M. P. l 22523QC.

(NH band 3.01 C haract. IR abs.

(C O ester band 5.89 (C=O amide band 5.92

. EXAMPLE x1 I00 g of polyvinyl chloride. 35 g of dioctyl phthalate. 2 g of a commercially available barium-cadmium stabilizer which is a barium-cadmium-laurate-myristate mixture (Estabex BC-l48) and 200 mg of compound (6) were mixed on a roll mixer at 180C. until a homogeneous, colorless, transparent sheet was obtained. This sheet was pressed to a uniform thickness of 0.2 mm. Subsequently, it was subjected to ultraviolet radiation in a Xenotester for 2,000 hours. Next, the degradation was determined visually and rated according to numerical scale ranging from 0 to 6, wherein the value 0 indicates that no degradation had taken place.

In an analogous way, the stabilizing power of other compounds according to the present invention was determined. The compounds used and the degradation measured are listed in Table 6.

TABLE 6 Compound None (I) (45) (4) (5) (46) (6) (30) (47) (control) Degradation 6 1 V2 7 l /2 i 2 1 V2 3 l l /2 3 (l0) (9). I (7) 3 v2 3 3 2 /2 2 /2 2 1 /2 1 /2 I 1 2 l 1 3 1 1 v2 1 v. 2

washing with water, the solvent was distilled off and recrystallized from hexane. 2.84 g of compound (37) having the formula given below (R 2 C H were obtained.

EXAMPLE XII g of high-density polyethylene were mixed with 250 mg of compound (7) and worked up on a roll 0.40 respectively.

EXAMPLE Xill 100 g of polystyrene and 0.2 g of compound l were mixed on a roll mixer at 130C. until a homogeneous, colorless, transparent sheet was obtained. This sheet was pressed to a uniform thickness of 0.2 mm. Subsequently it was subjected to ultraviolet radiation in a Xenotester for 2,000 hours. Next, the degradation was determined in the way described in Example Xl. This was 3. A sheet stabilized with compound and a non-stabilized sheet had a degradation of 4 and 6 respectively.

EXAMPLE XIV 100 g of unsaturated polyester resin, 2 g of a commercially available organic peroxide which is a mixture of benzoyl peroxide (50% by weight) and dimethylphthalate (Lucidol) and 0.2 g of compound (2) were mixed and poured into a sheet with a uniform thickness of 1 mm. This sheet was hardened for 2 hours at about 90C. and subsequently subjected to ultraviolet radiation in a Xenotester for 2000 hours. Next, the degradation was determined in the way described in Example XI. This was 4. A sheet stabilized with compound (I and a non-stabilized sheet had a degradation of 4 and 6 respectively.

What is claimed is:

1. The compound N,N'-bis(p-phenoxycarbophenyl sulfondiamide. 

1. THE COMPOUND N,N''-BIS(P-PHENOXYCARBOPHENYL SULFONDIAMIDE. 